Asymmetric Michael addition of 4H-thiopyran-4-one to nitroolefins catalyzed by diamine mono-N-sulfonamide and its application to concise synthesis of enantiopure multiring heterocycles

Tetrahedron

Volumn 69, Issue 33, 2013, Pages 6897-6905

  Mo, Lei ^a   Tang, Huang ^a   Yao, Zhu Jun ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

2 Bipyrrolidine; 4H Thiopyran 4 one; Heterocycle; Michael addition; Organocatalysis

Indexed keywords

3 ((R) 1 (BENZO [D][1,3] DIOXOL 5 YL) 2 NITROETHYL) DIHYDROTHIOPYRAN 4 ONE; 3 ((R) 1 (NAPHTHALEN 1 YL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(2 BROMO 4 FLUOROPHENYL) 2 NITROETHYL) DIHYDROTHIOPYRAN 4 ONE; 3 ((R) 1(2 BROMOPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(2 CHLORO 6 FLUOROPHENYL) 2 NITROETHYL) DIHYDROTHIOPYRAN 4 ONE; 3 ((R) 1(2 CHLOROPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(2 METHOXYPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(2,4 DICHLOROPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(2,4 DIMETHOXYPHENYL) 2 NITROETHYL) DIHYDROTHIOPYRAN 4 ONE; 3 ((R) 1(3 BROMOPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(3 CHLOROPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(3 METHOXYPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(4 BROMOPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(4 CHLOROPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 1(4 METHOXYPHENYL) 2 NITROETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 2 NITRO 1 PHENYLETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 2 NITRO 1(2 (TRIFLUOROMETHYL) PHENYL) ETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 2 NITRO 1(4 TOLYL) ETHYL) DIHYDRO THIOPYRAN 4 ONE; 3 ((R) 2 NITRO 1[4 (TRIFLUOROMETHYL) PHENYL) ETHYL] DIHYDROTHIOPYRAN 4 ONE; 3 ((S) 2 NITRO 1 (THIOPHEN 2 YL) ETHYL) DIHYDRO THIOPYRAN 4 ONE; 4H THIOPYRAN 4 ONE; ALKENE DERIVATIVE; DIAMINE DERIVATIVE; HETEROCYCLIC COMPOUND; MONO N SULFONAMIDE; NITROOLEFIN DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONAMIDE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 84879844425     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.116     Document Type: Article

References (104)

1. J. Aleman, and S. Cabrera Chem. Soc. Rev. 42 2013 774 793
2. P. Chauhan, and S.S. Chimni Beilstein J. Org. Chem. 8 2012 2132 2141
3. C. Palomo, M. Oiarbide, and R. Lopez Chem. Soc. Rev. 38 2009 632 653
4. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638 4660
5. X. Yu, and W. Wang Org. Biomol. Chem. 6 2008 2037 2046
6. C.H. Luo, and D.M. Du Synthesis 2011 1968 1973
7. N. Mase, and C.F. Barbas Org. Biomol. Chem. 8 2010 4043 4050
8. J.G. Hernandez, and E. Juaristi Chem. Commun. 2012 5396 5409
9. P.I. Dalko Angew. Chem., Int. Ed. 43 2004 5138 5175
10. P.I. Dalko Enantioselective Organo-catalysis 2007 Wiley-VCH Weinheim, Germany
11. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471 5569
12. H. Zhang, X.J. Wen, L.H. Gan, and Y.G. Peng Org. Lett. 14 2012 2126 2129
13. T. Kano, R. Sakamoto, M. Akakura, and K. Maruoka J. Am. Chem. Soc. 134 2012 7516 7520
14. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, and P. Melchiorre Angew. Chem., Int. Ed. 48 2009 7892 7894
15. J. Franzén, and A. Fisher Angew. Chem., Int. Ed. 48 2009 787 791
16. Y. Zhang, Y.K. Liu, T.R. Kang, Z.K. Hu, and Y.C. Chen J. Am. Chem. Soc. 130 2008 2456 2457
17. E.A. Peterson, and E.N. Jacobsen Angew. Chem., Int. Ed. 48 2009 6328 6331
18. C.K. De, E.G. Klauber, and D. Seidel J. Am. Chem. Soc. 131 2009 17060 17061
19. T. Bui, S. Syed, and C.F. Barbas J. Am. Chem. Soc. 131 2009 8758 8759
20. C. Uyeda, and E.N. Jacobsen J. Am. Chem. Soc. 130 2008 9228 9229
21. S.E. Reisman, A.G. Doyle, and E.N. Jacobsen J. Am. Chem. Soc. 130 2008 7198 7199
22. M. Ganesh, and D. Seidel J. Am. Chem. Soc. 130 2008 16464 16465
23. K.M. Steward, M.T. Corbett, C.G. Goodman, and J.S. Johnson J. Am. Chem. Soc. 134 2012 20197 20206
24. C.B. Jacobsen, L. Albrecht, J. Udmark, and K.A. Jørgensen Org. Lett. 14 2012 5526 5529
25. I. Piel, M. Stein-metz, K. Hirano, R. Frohlich, S. Grimme, and F. Glorius Angew. Chem., Int. Ed. 50 2011 4983 4987
26. Y. Suzuki, A. Md, T. Tanoi, N. Nomura, and M. Sato Tetrahedron 67 2011 4710 4715
27. J. Mahatthananchai, P.G. Zheng, and J.W. Bode Angew. Chem., Int. Ed. 50 2011 1673 1677
28. T. Jousseaume, N.E. Wurz, and F. Glorius Angew. Chem., Int. Ed. 50 2011 1410 1414
29. L. Lykke, K.S. Halskov, B.D. Carlsen, V.X. Chen, and K.A. Jørgensen J. Am. Chem. Soc. 135 2013 4692 4695
30. Y. Liu, S. Shirakawa, and K. Maruoka Org. Lett. 15 2013 1230 1233
31. O. Mahe, I. Dez, V. Levacher, and J.F. Briere Angew. Chem., Int. Ed. 49 2010 7072 7075
32. R.J. He, C.H. Ding, and K. Maruoka Angew. Chem., Int. Ed. 48 2009 4559 4561
33. R.J. He, X.S. Wang, T. Hashimoto, and K. Maruoka Angew. Chem., Int. Ed. 47 2008 9466 9468
34. O.M. Berner, L. Tedeschi, and D. Enders Eur. J. Org. Chem. 2002 1877 1894
35. N. Krause, and A. Hoffmann-Roder Synthesis 2001 171 196
36. S.B. Tsogoeva Eur. J. Org. Chem. 2007 1701 1716
37. D. Almasi, D.A. Alonso, and C.N. Ajera Tetrahedron: Asymmetry 18 2007 299 365
38. B. List, P. Pojarliev, and H.J. Martin Org. Lett. 3 2001 2423 2425
39. J.M. Betancort, K. Sakthivel, R. Thayumanavan, and C.F. Barbas III Tetrahedron Lett. 42 2001 4441 4444
40. J.M. Betancort, and C.F. Barbas III Org. Lett. 3 2001 3737 3740
41. S. Hanessian, and V. Pham Org. Lett. 2 2000 2975 2978
42. D. Enders, and A. Seki Synlett 2002 26 28
43. Y.G. Chiand, and S.H. Gellman Org. Lett. 7 2005 4253 4256
44. S. Moss' e, and A. Alexakis Org. Lett. 7 2005 4361 4364
45. C.E.T. Mitchell, A.J.A. Cobb, and S.V. Ley Synlett 2005 611 614
46. A. Alexakis, and O. Andrey Org. Lett. 4 2002 3611 3614
47. N. Mase, R. Thayumanavan, F. Tanaka, and C.F. Barbas III Org. Lett. 6 2004 2527 2530
48. T. Ishii, S. Fujioka, Y. Sekiguchi, and H. Kotsuki J. Am. Chem. Soc. 126 2004 9558 9559
49. J.M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, and C.F. Barbas III Synthesis 2004 1509 1521
50. O. Andrey, A. Alexakis, A. Tomassini, and G. Bernardinelli Adv. Synth. Catal. 346 2004 1147 1168
51. A.J.A. Cobb, D.A. Longbottom, D.M. Shaw, and S.V. Ley Chem. Commun. 2004 1808 1809
52. A.J.A. Cobb, D.M. Shaw, D.A. Longbottom, J.B. Gold, and S.V. Ley Org. Biomol. Chem. 3 2005 84 96
53. W. Wang, J. Wang, and H. Li Angew. Chem., Int. Ed. 44 2005 1369 1371
54. N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, and C.F. Barbas III J. Am. Chem. Soc. 128 2006 4966 4967
55. C.-L. Cao, M.-C. Ye, X.-L. Sun, and Y. Tang Org. Lett. 8 2006 2901 2904
56. E. Reyes, J.L. Vicario, D. Badia, and L. Carrillo Org. Lett. 8 2006 6135 6138
57. J. Wang, H. Li, B. Lou, L. Zu, H. Guo, and W. Wang Chem. - Eur. J. 12 2006 4321 4332
58. S.V. Pansare, and K. Pandya J. Am. Chem. Soc. 128 2006 9624 9625
59. Vishnumaya, and V.K. Singh Org. Lett. 9 2007 1117 1119
60. B. Ni, Q. Zhang, and A.D. Headley Tetrahedron: Asymmetry 18 2007 1443 1447
61. D.-Q. Xu, L.-P. Wang, S.-P. Luo, Y.-F. Wang, S. Zhang, and Z.-Y. Xu Eur. J. Org. Chem. 2008 1049 1053
62. B.-K. Ni, Q.-Y. Zhang, K. Dhungana, and A.D. Headley Org. Lett. 11 2009 1037 1040
63. C. Chang, S.-H. Li, R.J. Reddy, and K. Chen Adv. Synth. Catal. 351 2009 1273 1278
64. R.J. Reddy, H.-H. Kuan, T.-Y. Chou, and K. Chen Chem. - Eur. J. 15 2009 9294 9298
65. M. Wiesner, M. Neuberger, and H. Wennemers Chem. - Eur. J. 15 2009 10103 10109
66. S.-L. Zhu, S.-Y. Yu, and D.-W. Ma Angew. Chem., Int. Ed. 47 2008 545 548
67. D.-Z. Xu, S.-S. Shi, Y.-J. Liu, and Y.-M. Wang Tetrahedron 65 2009 9344 9349
68. S. Saha, S. Seth, and J.N. Moorthy Tetrahedron Lett. 51 2010 5281 5286
69. X.-Y. Cao, J.-C. Zheng, Y.-X. Lia, Z.-C. Shua, X.-L. Sun, B.-Q. Wang, and Y. Tang Tetrahedron 66 2010 9703 9720
70. J. Agarwal, and R.K. Peddinti Tetrahedron Lett. 52 2011 117 121
71. D.-F. Lu, Y.-F. Gong, and W.-Z. Wang Adv. Synth. Catal. 352 2010 644 650
72. M. Yoshida, A. Sato, and S. Hara Org. Biomol. Chem. 8 2010 3031 3036
73. N.A. Paras, and D.W.C. MacMillan J. Am. Chem. Soc. 123 2001 4370 4371
74. N. Halland, R.G. Hazell, and K.A. Jørgensen J. Org. Chem. 67 2002 8331 8338
75. T. Okino, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 125 2003 12672 12673
76. N. Halland, T. Hansen, and K.A. Jørgensen Angew. Chem., Int. Ed. 42 2003 4955 4957
77. P. Melchiorreand, and K.A. Jørgensen J. Org. Chem. 68 2003 4151 4157
78. H. Li, Y. Wang, L. Tang, and L. Deng J. Am. Chem. Soc. 126 2004 9906 9907
79. S.B. Tsogeva, and S.-W. Wei Chem. Commun. 2006 1451 1453
80. S.-W. Wei, D.A. Yalalov, S.B. Tsogoeva, and S. Schmata Catal. Today 121 2007 151 157
81. H.-B. Huang, and E.N. Jacobsen J. Am. Chem. Soc. 128 2006 7170 7171
82. S. Luo, X. Mi, L. Zhang, S. Liu, H. Xu, and J.-P. Cheng Angew. Chem., Int. Ed. 45 2006 3093 3097
83. C.G. Kokotosand, and G. Kokotos Adv. Synth. Catal. 351 2009 1355 1362
84. T. Inokuma, Y. Hoashi, and Y. Takemoto J. Am. Chem. Soc. 128 2006 9413 9419
85. X.-X. Jiang, Y.-F. Zhang, A.S.C. Chan, and R. Wang Org. Lett. 11 2009 153 156
86. Y. Hayashi, H. Gotoh, T. Hayasi, and M. Shoji Angew. Chem., Int. Ed. 44 2005 4212 4215
87. C. Palomo, S. Vera, A. Mielgoand, and E. Gomez-Bengoa Angew. Chem., Int. Ed. 45 2006 5984 5987
88. M. Lombardo, M. Chiarucci, A. Quintavalla, and C. Trombini Adv. Synth. Catal. 351 2009 2801 2806
89. K. Liu, H.-F. Cui, J. Nie, K.-Y. Dong, X.-J. Li, and J.-A. Ma Org. Lett. 9 2007 923 925
90. A. Lu, P. Gao, Y. Wu, Y. Wang, Z. Zhou, and C.-C. Tang Org. Biomol. Chem. 7 2009 3141 3147
91. M. Freund, S. Schenker, and S.B. Tsogoeva Org. Biomol. Chem. 7 2009 4279 4284
92. Y.-F. Ting, C. Chang, R.J. Reddy, D.R. Magar, and K. Chen Chem. - Eur. J. 16 2010 7030 7038
93. F. Yu, Z.-C. Jin, H.-C. Huang, T.-T. Ye, X.-M. Liang, and J.-X. Ye Org. Biomol. Chem. 8 2010 4767 4774
94. R. Husmann, M. Jorres, G. Raabe, and C. Bolm Chem. - Eur. J. 16 2010 12549 12552
95. A.M. Flock, A. Krebs, and C. Bolm Synlett 2010 1219 1222
96. T.C. Nugent, M. Shoaib, and A. Shoaib Org. Biomol. Chem. 9 2011 52 56
97. X.-H. Ding, X. Li, D. Liu, W.-C. Cui, X. Ju, S.-z. Wang, and Z.-J. Yao Tetrahedron 68 2012 6240 6248
98. X.-H. Ding, W.-C. Cui, X. Li, X. Ju, D. Liu, S.-z. Wang, and Z.-J. Yao Tetrahedron Lett. 54 2013 1956 1959
99. X.-N. Song, and Z.-J. Yao Tetrahedron 66 2010 2589 2593
100. M.D. Pierce, R.C. Johnston, S. Mahapatra, H. Yang, R.G. Carter, and P.H.-Y. Cheong J. Am. Chem. Soc. 134 2012 13624 13631
101. R. Huisgen Angew. Chem., Int. Ed. Engl. 2 1963 565 598
102. L.I. Smith Chem. Rev. 38 1938 193 285
103. J. Hamer, and A. Macaluso Chem. Rev. 64 1964 473 495
104. J. Yang Synlett 2012 2293 2297